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How To Be Less Old · Aug 25, 2026

Olivia Rodrigo’s Thoroughly Modern Lilith Fair

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Deanna Cheng, How To Be Less Old, Emily Freda Foster · How To Be Less Old

On today’s pod, Deanna reveals she’s gearing up to try a new way of interacting with youths in the wild, in an effort to combat the Gen Z stare. Emily, meanwhile, is on the hunt for the breeziest pant to carry her through these early back-to-school days.

They also investigate how the Tabi, aka the horse-hoof shoe, came to be and whether it might secretly be the most comfortable shoe on the market.

These three shoe styles really burn their buns: Sneex, Sneakerina and Tabi

Plus, they dive deeper into generational trends and confirm they are card-carrying members of Gen X, even if one is planted firmly in the middle while the other is hanging on by the final birth year.

And! Emily is braving her first music festival with her daughter Este! The festival is called Daisy Chain Fields and it’s being presented by Olivia Rodrigo. A new girl-powered festival, is the Gen Z answer to Lilith Fair, and the lineup is pure lady power.

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Read the original on howtobelessold.substack.com

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